Please note that masks are required in the village and that many of the locations listed below have their own policies, which should be reviewed before visiting.
1. Experience life on the farm
Woodstock offers a double-whammy of Sugarbush Maple and Cheese Farm (free samples? Yes, please!) and Billings Farm & Museum, one of the finest outdoor history museums—and a fully-functional farm, at that! Gather the whole family to say hello to friendly animals, snag an inside look at how things are made, discover hidden gems on hundreds of acres, and even partake in a round of pumpkin bowling—all under a vibrant canopy of leaves! Welcome to farm country.
Autumn... the year's last, loveliest smile
2. Pick-your-own apples on Vermont’s hillside orchards
No need to upset the applecart on your autumnal plans—because you can still enjoy this pastoral adventure in the crisp, cool air! Click here to learn about two orchards within 15 minutes of Woodstock, their policies, hours, and more.
3. Hike it out
With the recent addition of the Ottauquechee River Trail, Woodstock is more walkable than ever—offering one of the best ways to experience fall foliage! Pick your path from a quick stroll through the town green to a steep hike up Mt Tom for a panoramic view of the quaint village below—and everything in between. Click here for a list of hiking options, trail-maps, and more.
4. Catch a flick or concert under the September sky
Pull up a (lawn chair), grab a blanket, and don’t forget to bring the popcorn—because movie and music nights have moved outdoors! But you’ve got to act fast. Only a few weeks remain for Pentangle Arts’ September Movie Series on the North Chapel’s back lawn and dance-worthy live performances at Feast & Field in nearby Barnard—and both events are reservation only.
5. Try your hand at the sport of kings
There’s nothing like watching a Harris's Hawk take flight, opening its 47” wingspan, its reddish brown feathers blending with the vibrant foliage below.
6. Take to Woodstock’s beautiful back-roads by car for a stunning foliage tour
Dream of driving through a tunnel of yellows, oranges, and reds, gravel crunching under your tires? Woodstock’s country roads are calling, with plenty of scenic vistas and jaw-dropping estates to fill your Instagram for months to come. Click here for local artist and photographer Judy Laliberte’s tips and favorite spots to snap.
7. Shop local
Admiring our historic storefronts and perusing the wares of lovely mom-and-pop shops is a pastime all its own! Many of our shops are open for (in-person) business, just be sure to wear a mask both on the village sidewalks and within each business.
8. Grab the reins in horse country
Saddle up for everything equestrian, from fall foliage pleasure rides across miles-and-miles of dirt roads, wooded trails, and meadows to an autumnal dressage show with The Green Mountain Horse Association (GMHA) nestled in bucolic South Woodstock. Don’t forget your riding boots and bridles. We’re not horsing around on this one.
9. Immerse yourself in the trees at the VINS Canopy Walk
The Vermont Institute of Natural Science (VINS) in nearby Quechee is a nature lover’s wonderland, and the Canopy Walk, added in 2019, takes the nature center to new heights. Between visiting rehabilitated birds in their outdoor enclosures and learning what it takes to care for these fascinating fowl, take to the treetops via an ADA-accessible boardwalk that rises as high as 81 feet (or four giraffes) above the forest floor, affording panoramic views of autumn’s colorful display, Dewey’s Mill Pond, and beyond.
10. Take farm-to-table literally
Inside the spectacular Red Barn at Kelly Way Gardens, dine on the produce plucked fresh from the grounds, brought together with local cheeses, honey, dairy, and more via menus handcrafted by Woodstock Inn & Resort Executive Chef Rhys Lewis. But don't delay, because this reservation-only dinner series concludes in September!
11. Get creative virtually or in-person with Artistree’s classes
You can dance if you want to—or paint, write, cook, perform, and create in endless ways because Artistree’s fall classes are in session! Artists of all ages can join in on the activities at the socially-distanced campus or log on from home, but please read Artistree’s health and safety policy here before registering.